


First Time Insecurities

by getwaytooinvolved



Category: Shawn Mendes (Musician)
Genre: F/M, First Time, Smut
Language: English
Status: Completed
Published: 2018-12-30
Updated: 2018-12-30
Packaged: 2019-09-30 19:20:52
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,320
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17229728
Author URL: https://archiveofourown.org/users/getwaytooinvolved/pseuds/getwaytooinvolved
Summary: You hesitated for a long moment, knowing exactly that you had ruined the mood already. “I guess I’m insecure” You admitted with another shrug. His eyebrows raised, complete surprise written in his warm eyes. “About what?” He asked, the tone in his voice clearly implying that he had no idea what you were talking about.***********Reader is insecure about her body and Shawn shows her that he loves all of her





	First Time Insecurities

Your head tilted back with a deep sigh, his lips on your neck leaving soft kisses behind that lingered longer with each new one until he parted his lips and sucked on the skin right below your earlobe. He had asked you to come over to his condo that night for dinner and movies and had shyly suggested that you could stay the night again. It had happened a few times that you stayed at his place or he ended up staying at yours for the night, but nothing had happened between you yet. You often wondered if he minded that you hadn’t had sex yet, but he had never given you the feeling like he wanted to take things further. But something was different tonight. So when you found yourself straddling his lap halfway through the movie you wondered if you would finally build up the courage to take it all the way or if it would end with a heavy make out session and wandering hands like a couple of previous nights.

Your hands grasped at his hair as your mouth fell open with a soft gasp, your chest arching into his and his hands tightening on your hips. His name left your lips in barely more than a breath, trying to shift closer to him and only ending up grinding against him, feeling his hardening length pressing against your leg through his sweatpants. “Fuck, baby” He groaned lowly and moved to nibble on your earlobe, a shiver running down your spine and his hands lightly digging into your hips, guiding them to move against his. His head lifted, finding your lips in a rushed and passionate kiss as his hips lightly rocked off the couch to meet yours, creating a gentle friction that had your head spinning with lust.

You couldn’t help the soft whimper from escaping your throat at the feeling of his teeth sinking into your bottom lip, tugging at it and nibbling on the sensitive skin. His legs spread a little further, making it even more comfortable for you on his lap as he slowly pulled away from you and looked at you with darkened eyes, quickened breaths leaving both of your parted lips and mixed with the others.

He knew you didn’t have a lot of experience, could clearly remember that night when you had confessed it to him with blushing cheeks and trembling hands. “Stop me if I go too far” He mumbled, his grip on your hips loosening and his hands moving to rest around your waist, his head lowering to bury into your chest, pushing your low cut top down a little in the process. His hands cupped your boobs at the moan that left your lips, your eyes falling shut as you tightly held onto his shoulders, completely concentrating on the feeling of his lips on your skin.

Your back arched into his touch as he pulled both your top and cup of your bra down just enough to attach his mouth to your nipple, one of his hands landing on your butt to press your crotch against his when a whimper fell from your mouth. “Shawn” You moaned softly, successfully getting his attention as he opened his eyes to look up to you, not stopping his teeth from gently tugging on your nipple. “Bedroom, please” You begged, the sight of his lips attached to your chest making your core throb with want. He grinned against your skin, his eyes still not leaving yours as he licked over the hardened bud a few times before he slowly pulled back, your clothes falling back into place.

He held you in place as you wanted to get up, worry written in his eyes. “You’re sure?” He whispered, his hands resting on your thighs as he looked at you with the most sincere expression that you had ever seen.

“Absolutely” You nodded and leaned in to place a short peck on his lips. His hands left your body, allowing you to get up and following you into the bedroom where he swiftly picked you up, grinning at the surprised squeal that filled the bedroom. Crawling onto the bed, he carefully lowered you down onto the mattress so your head landed perfectly on the pillows, his broad body hovering over you.

He nosed along your jaw in a way that was playful and yet loving, your quiet giggle filling the bedroom as you squirmed underneath him and lightly pushed at his chest. “Can we-” He placed a soft kiss behind your ear. “Do you mind if I turn a light on?” He murmured and slowly trailed a hand up and down your side. You swallowed heavily and let your eyes fall shut as he placed chaste kisses over your neck, your head titling back. He blindly reached over and turned the small bedside lamp on that engulfed the room in a warm glow. His lips captured yours in a rather tender and loving kiss, one hand braced on the side of your head and the other placed on your cheek, your hips trapped between his knees. “Like this? Or is it too much?”

“It’s okay” You whispered and nodded. He gave you a soft smile and combed his hand through your hair before he found your lips in another kiss. He had promised himself to take it slow when you had told him that you were a virgin and he had no intentions of breaking that promise now. Your hands ran down his back to tug at the hem of his T-shirt, his lips breaking away from yours as he grabbed the collar and pulled the fabric over his head, tossing it aside carelessly.

“No rushing, yeah? We’ve got all night” He whispered against your neck where he trailed soft kisses over your skin, easily finding the spot that he had attacked earlier. You nodded, exhaling shakily as he shifted down your body and forcing your eyes to watch him. His hands slipped underneath your top, his lips immediately finding the exposed skin and covering it in chaste kisses.

You tensed up beneath him as he slowly kneaded your hips in his hands, suddenly feeling insecure with his muscled body over your curvy one. He seemed to notice as he pulled his hands away and moved up again to place a handful of chaste kisses over your jaw. “Can we get under the covers?” You asked quietly and felt him stop, your heart dropping in fear of having said the wrong thing.

But then he placed a peck on your jawbone and pushed himself up. “Of course we can” He nodded and climbed off the bed, helping you up before he tugged the sheets back and let you get beneath them. He followed and laid on his side facing you, simply watching you for a moment before he reached out for you. His arm placed under your neck as you shifted closer, the other wrapping around your waist while he rested his forehead against yours. “Why do I get the feeling like you’re forcing yourself to do this?” He asked, his voice soft with a hint of confusion. His hand slowly trailed up and down your side while he patiently waited for you to answer.

“I’m not” You responded and let a hand trace over his defined chest and stomach, feeling the muscles tense under your fingertips. “Promise” You added when he kept looking at you. “I’m just…” You trailed off and shrugged, his hand moving from your waist to your face. He tilted your chin up as you avoided his eyes, gently forcing you to look at him.

“You’re what?”

You hesitated for a long moment, knowing exactly that you had ruined the mood already. “I guess I’m insecure” You admitted with another shrug.

His eyebrows raised, complete surprise written in his warm eyes. “About what?” He asked, the tone in his voice clearly implying that he had no idea what you were talking about.

You felt your cheeks heat up. “Like… Like my hips” You said.

His hand moved down to rest on your hip, fingers gently digging into the flesh and noticing the way you tried to squirm away. “These?” He asked quietly, a slow smile spreading over his lips as you nodded. “But why?”

“There’s too much fat” You answered and watched in confusion as he wormed his way beneath the covers, disappearing beneath them. You held your breath as you felt him push your top up to your stomach, warm lips touching the exposed skin seconds later.

“But, honey” His voice was slightly muffled. “They’re perfect. I couldn’t do this if they weren’t like that”

You gasped as his teeth were suddenly digging into your skin, tongue soothing over the spot before he sucked, intent on leaving a mark behind. He manhandled you to lay on your back so he had access to the other side too, but didn’t leave another mark there.

You hadn’t even noticed that he had climbed on top of you until you became aware of his weight as he moved up your body again. Your soft giggle filled the room as his face appeared moments later, covers still draped over his head as he looked at you with a proud grin. “What else?”

You shook your head and pushed the covers down to his shoulders, revealing his messy curls. “Let’s just-”

“What else?” He interrupted you.

You bit your bottom lip and ran a hand through his hair, pushing it back. “My thighs. They’re huge and I got stretch marks on them”

He silently looked at you long enough to make you feel insecure before he spoke up. “Can I take your sweatpants off?”

You fiddled with his necklace and nodded slowly. “Yeah” You whispered, barely managing to return the quick kiss he placed on your lips before he disappeared beneath the sheets again. You grinned and ran a hand through your hair, feeling his fingers hooking into the waistband of your sweats before he tugged them down.

“Please don’t kick me in the face with your knee” He said while clumsily pulling the fabric off your legs, carelessly pushing them off the bed. “Shit, it’s dark down here” He giggled, his hands slowly moving up the outside of your thighs. You let your eyes fall closed as he gently coaxed you to spread your legs, his warm lips touching the inside of your thighs seconds later- right where you knew the stretch marks were. You were so thankful that he couldn’t see you blushing, your breath hitching in your throat as he got dangerously close to your panties before he moved to the other side.

His hands were everywhere, gripping your thighs and hips before moving his fingertips over your skin in a touch that left goosebumps behind before he gripped them again. Your eyes opened when he suddenly released a sound that was close to a growl. “What?” You asked alarmed.

You only felt his hands on your hips and his breath on the inside of your thigh as you stared up at the ceiling. “Nothing” He breathed and this time kissed further up your thigh until he felt the edge of your panties at the corner of his mouth. “You just smell amazing” He mumbled against your skin, his lips suddenly on your panties just an inch above your clit. His thumbs toyed with the waistband as you gasped loud enough for him to hear. “Can I-?”

“Yes, please. Yes” You rushed out, your fingers curling into the covers and tugging as his tongue was suddenly pushing against your clit with the fabric of your panties still separating you. You squirmed beneath him, your eyes squeezing shut. “Shawn, please”

“Yeah?”

“Yes, I’m sure. Please, just…” You trailed off as you felt him pull your panties down before his lips were on your thighs again. You exhaled loudly and bit your bottom lip, reaching below the covers and tangling your hands into his hair to guide him to your core. He chuckled quietly before his mouth was finally,  _finally_  where you wanted him. You mewled as he licked a slow stripe up to your clit that he circled with the tip of his tongue, drawing a breathless gasp from you before he pulled back. His hands pushed your thighs up so your legs bent at your knees, feet flat on the mattress and giving him enough space to fit his broad shoulders under your legs. You hurried to push the covers down enough to be able to see him, comfortably settled between your legs and his mouth on your core again. His darkened eyes looked up to you as he sucked on your clit, one arm wrapping around your thigh and hand placing flat on your stomach right below where your top was still bunched up.

With a soft sigh you let your head drop back to the pillow, one hand tangling into his hair again while the other placed on top of his on your stomach. He immediately twisted his wrist to intertwine your fingers, the sight of you laid out in front of him from that angle making him completely hard trapped underneath his clothes. Your stomach tensed and you let out a quiet whimper as one of his fingers was suddenly slowly pushing into you. It didn’t take long until he added another one, crooking them and caressing your walls in ways that had your head spinning with his mouth still working your clit. His fingers reached so much deeper than yours and reached spots you had never managed to explore before, your body heating up as he slowly worked you closer to your orgasm. “Baby?” He murmured, his lips brushing your clit as he talked.

You lifted your head off the pillow to look at him, biting your bottom lip at the sight that greeted you. His mouth and chin were glistening and his eyes were blown wide, his fingers still moving inside of you. “What?” You breathed.

“Can you take those clothes off for me?” He asked and lowered his head down again, his hand placing around your thigh as you untangled your fingers from his. His tongue licked over your clit as he watched how you pulled the top up over your head and tossed it aside. “Bra too?” He suggested in a gentle voice, squeezing your thigh when you hesitated. “What’s wrong?”

“I also have stretch marks on my boobs” You told him, your cheeks heating up again. Placing a kiss on your lower stomach, he pushed himself up to hover over you. His thumb took place of where his mouth had been just seconds ago, rubbing perfectly placed circles over your clit in time with his fingers crooking and pulling and pushing.

His head tilted to your chest, lips placing light kisses over the skin he could reach, along the edge of the cup and over to the other one. “How many times-” He whispered, interrupting himself by placing more kisses up to your neck. “Do I have to show you-” He continued, moving to your ear and nibbling on your earlobe. “That I love you the way you are?”

Reaching below yourself, you undid the clasp with slightly trembling fingers, the thought of being completely exposed beneath him making you a little nervous. And yet you brushed the straps off your shoulders and tossed the bra away, gasping when he immediately lowered his head to your chest again. He placed kiss after kiss on every single stretch mark he found before he attached his lips to one and started sucking, leaving a hickey on the side of your breast. “Oh” You breathed when he brushed his lips over your hardened nipples in the faintest touch, his gaze staying on yours as he slowly moved down your body again while leaving a trail of soft kisses over your skin.

He skipped the slow pace he had gone before and instead eagerly wrapped his lips around your clit again, twisting and crooking his fingers to brush the spot he had only teased earlier. “ _Oh_ ” Your body jolted in surprise and your hand reached for his hair again as you tugged on it. He watched you with darkened eyes, took in the way your breathing sped up and the way you writhed against the sheets, the way you tensed up before you came with a quiet whimper of his name.

He worked you through it, feeling himself throb and leak in his boxers as he greedily watched you until you relaxed and took a shaky breath. You whimpered when he slowly pulled his fingers out of you, your head tilting to look at him as he sat up between your legs and brought his hand up, licking his fingers clean. You tried to cover yourself with your hands as he let his gaze trail over your body, his head shaking and hands placing on your thighs where he caressed your stretch marks again. “You’re so beautiful” He whispered and reached for your wrists, gently pulling your hands away while he leaned down.

His lips peppered tender kisses over your neck and jaw when he felt you reach down, your nails just lightly scratching down his chest in a way that had goosebumps breaking out all over his skin before you reached the waistband of his sweatpants. He didn’t stop kissing your neck, letting you go on your own pace. He let you fiddle with the strings and gave you a sound of satisfaction when you slowly explored the dented front of his sweats, your hand curling around his cock for a moment before you pulled your hand back again. All words of encouragement for you to keep going got stuck in his throat as you hooked your fingers into both the waistband of his sweatpants and boxers, his head lifting to nibble on your earlobe while you pushed the rest of his clothes down as far as you could reach. He sucked in a breath as his hard length sprung free, the tip grazing your thigh and giving him just a second of relief.

Trying to not be too clumsy while he kicked his clothes off, he carelessly pushed them off the bed with a shove of his foot before he turned his full attention back to you. Your eyes were on his chest, your cheeks a bit flushed. “You okay?” He whispered and gave you a soft smile as you looked at him.

You returned it, your hands coming up to rest on his strong shoulders. “Mhm. I just noticed that we never talked about protection”

“I got that covered, don’t worry” He reassured you and placed a kiss on your forehead before he pushed himself up to reach over to the bedside table.

You let your eyes trail down his defined body, forcing yourself not to stare at his dick for too long. The words left your mouth before you could stop them, an immediate blush spreading over your cheeks. “I should return the favor right? I mean, you ate me out. I should blow you now”

He had a gentle smile playing on his lips as he came back with a shiny foil square between his fingers. “You don’t have to return any favors, first of all” He told you, sitting between your spread legs as he ripped the square open without taking his eyes off you. “I don’t expect you to. Especially not tonight when enough things are new for you- we really don’t have to add another thing to that” He only briefly took his eyes off you while he rolled the condom over himself with skilled fingers. “We’ll tackle that some other time when you feel like giving me a blowjob, alright?” He suggested and pulled the covers with him while he settled on top of you, holding himself up on his forearms on either side of you.

“Okay” You whispered and reached up to cup his face in your hands, pulling him down until he kissed you again.

He definitely didn’t fail to notice that you trembled slightly underneath him, pulling back to place a kiss on the sensitive spot just underneath your ear. “Hey” He whispered, his nose brushing against your ear. “It’s just me. Relax” He murmured, moving to place soft kisses along your shoulder. “I don’t care if we’re still here at 4 in the morning and nothing’s happened yet, okay?” He told you and looked at you. You returned the smile he gave you and nodded, tilting your head in a silent question for another kiss that he gladly gave you. One kiss turned into two, three, four, until you lost count of them.

He had you right where he had wanted you. Utterly relaxed beneath him, all the tension from before having slowly faded with each new kiss. One of your hands trailed down his back, settling on his lower back before you applied a bit of pressure. His lips tugged into a smile against yours as he followed your silent request. He pulled away from your lips to instead place a couple of soft kisses over your cheek while he reached between your bodies. “Promise you’ll tell me if something doesn’t feel right? No matter if you’re hurt or you’re uncomfortable or just changed your mind?” He whispered, receiving an immediate nod from you.

“Promise” You breathed and shifted beneath him, his tip brushing through your folds and pulling a gasp from you. Your toes curled as you felt his tip stretch you open before he thrust into you with a slow movement. You sucked in a breath and squirmed beneath him, the feeling so foreign and yet ecstatic. Reading your reaction wrong, he stopped in his movements and braced both of his arms beside you again. “No, keep going. I’m okay” You whispered. Your back arched off the bed as he pushed the rest of the way in, your chest rising and falling quickly and your hands grasping at his biceps. He was biting his bottom lip and his eyes were blown wide as he stopped when his hips were pressed up against yours. “Fuck, give me a second” You whispered, his length stretching you in the best way possible and throbbing against your tight walls.

He leaned his forehead against yours and forced himself to stay unmoving, resisting the urge to slam his hips against yours over and over again until you screamed his name. He patiently waited until you nodded before he pulled back until only his tip was left inside before thrusting into you again. Your nails dug into his arms and your mouth opened without a sound coming out as he repeated the movement, soon settling on a gentle but deep pace that had both of you whimpering every now and then.

“Fuck, you feel so good” He moaned into your ear, thrusting as deep as possible into you and staying like that for a second before he pulled back again. His lips found yours in a slightly sloppy kiss, his movements never stopping while he released soft moans against your mouth. Your legs wrapped around his waist, creating a new angle that had him whimpering quietly. “I’m so not going to last long”

You giggled and brought your hands up to comb them through his hair, making him look at you. “That’s okay, don’t worry” You smiled and lifted your head off the pillow to capture his lips in a tender kiss. He slowed his movements, his hands reaching for yours and intertwining your fingers with his before stretching your arms above your head, resting your tangled hands on the pillow. You released a soft sound into his mouth as he quickened his thrusts, only encouraging him to keep going.

You tilted your head back as he placed a trail of kisses over your chin, down your neck to your chest where he wrapped his lips around one of your nipples. Your eyes closed and your hands squeezed his, chest arching into his mouth as he gently nibbled and tugged on the hardened bud before he switched to the other one. “ _Fuck_ ” He mumbled against your skin and moved to bury his face into your neck. You bit your bottom lip as he sucked near your collar bone and you knew exactly that he left a hickey behind, but you couldn’t bring yourself to complain. Deep down you wanted him to mark you, to show the world that you were his. “I’m so close already” He sighed and placed a kiss on the abused skin.

“Don’t hold back” You said and squeezed his hands again. A sudden surge of confidence rushed through your chest and the words left your mouth before you could talk yourself out of it. “Can you come for me, Shawn?”

For a second he was quiet before he groaned loudly and lifted his head, looking at you with heavy lidded eyes. “ _Jesus_ , you can’t just…” He trailed off and tightly bit his bottom lip. You tightened your legs around his waist and forced him deeper into you, a growl-like sound rumbling in his chest and his head lowering to rest in the crook of your neck again. It only took a few more deep thrusts before he stilled inside of you, his cock throbbing against your walls as he came with quiet moans that were muffled against your neck.

He slowly pulled out of you and noticed the way your legs around him tightened, a small smile spreading over his lips before he shifted to rest his head on your bare chest. Your hands untangled from his, moving them to comb your fingers through his slightly sweaty hair while his hands came to rest around your side, his thumbs tracing along the curve of your boobs as far as he could reach.

**Author's Note:**

> Come talk to me on Tumblr! @getwaytooinvolved


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